KR20200106450A - Colored composition, color filter using same, and use thereof - Google Patents

Abstract

The present invention is to provide a coloring composition capable of producing a color filter excellent in brightness, and a color filter produced by using the same. The coloring composition for the color filter containing a methane compound, a binder resin, and a dispersant is represented by chemical formula (1). In the chemical formula (1), each of R^1 to R^4 independently represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms, a methoxy group, or a nitro group. R^5 represents an alkyl group having 1 to 4 carbon atoms, a methoxyethyl group, or a butoxyethyl group. Each of R^6 to R^10 independently represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 6 carbon atoms, a methoxy group, an alkylcarbonylamino group having 1 to 3 carbon atoms, or -SO_3^-. However, at least one of R^6 to R^10 represents -SO_3^-.

Description

A colored composition, a color filter using the same, and its use TECHNICAL FIELD [COLORED COMPOSITION, COLOR FILTER USING SAME, AND USE THEREOF]

The present invention provides a colored composition containing a methine compound used when forming a green pixel of a color filter, a color filter formed using the colored composition, and a liquid crystal display device formed using the color filter, an imaging device ( CCD, CMOS), and an organic EL display.

Liquid crystal display devices such as liquid crystal displays (LCD) and organic EL displays typified by laptop computers, liquid crystal TVs, mobile phones, and smart phones, and image pickup devices (CCD, CMOS) used as input devices such as digital cameras and color copiers. Colorization requires color filters. As a method of manufacturing a color filter used for such a liquid crystal display device or a solid-state image sensor, there are a dyeing method, an electrodeposition method, a printing method, a pigment dispersion method, and the like, but recently, a pigment dispersion method using a patterning method has become mainstream. As a patterning method, a photolithography method is typical, and a color filter is formed using a mixture of a photosensitive resin composition and a pigment dispersion. In addition, in recent years, a method of forming a color filter by applying a colored ink directly onto a substrate by an inkjet printer without interposing a mask has also been performed.

It is particularly important to improve color purity, saturation, brightness and contrast, which are the properties required for color filters. By improving the brightness, it is possible to suppress the amount of light of the backlight, and as a result, power consumption is reduced, so it is an environmentally necessary technique. In order to improve the color purity of the color filter, it is necessary to increase the content of the color pigment or to select a pigment having a better spectral waveform. On the other hand, in order to improve the brightness, it is necessary to increase the transmittance by reducing the pigment concentration or thinning the film thickness. In order to achieve these contradictory properties, a method of micronizing pigments is being carried out, but there is a limit to the improvement of the dispersion stability of the coloring composition and the resistance and contrast of the color filter to light, heat, or solvents. The reality is that it is impossible to achieve balance of results.

As another approach for solving these problems, examination of a color filter using a dye is in progress. If a dye is used, there is an advantage in that the contrast can be improved because both color purity and brightness cannot be achieved with the pigment, and light scattering can be suppressed. However, on the other hand, excellent light resistance and heat resistance are required for display applications that require long-term reliability, such as for televisions, but dyes are generally inferior in resistance to pigments. Further, until now, the development of blue and red pigments for color filters has been actively conducted, but the number of green pigments is limited compared to the former. Among them, for example, Patent Documents 1 to 6 relate to a green color filter in which a green dye of phthalocyanine, a yellow dye of a complementary color, and a resin are combined. In addition, Patent Documents 7 and 8 relate to a green colored composition for color filters using a methine compound. However, these documents do not describe at all about the brightness of the color filter. In other words, it is a reality that the green color filter used in the field of display devices and solid-state imaging devices does not sufficiently satisfy the required characteristics of brightness.

Japanese Patent No. 5545313 Japanese Published Patent Publication No. 2018-17856 Japanese Published Patent Publication No. 2018-111757 Japanese Published Patent Publication No. 2018-169505 Japanese Published Patent Publication No. 2016-006137 Japanese Patent No. 6440494 Japanese Unexamined Patent Publication No. 2017-179177 Japanese Published Patent Publication No. 2018-154782

An object of the present invention is to provide a novel coloring composition capable of producing a high-quality and highly reliable color filter excellent in brightness, and a color filter manufactured using the same.

In order to solve the above problems, the inventors of the present invention have conducted extensive research and found that the above problems can be solved by using a colored composition containing a methine compound having a specific structure, and the present invention has been completed.

That is, the present invention is as follows.

(1) the following formula (1)

(In formula (1), R ¹ to R ⁴ each independently represent a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms, a methoxy group or a nitro group. R ⁵ is an alkyl group having 1 to 4 carbon atoms, or a methoxy group. which represents an ethyl group or a butoxy ethyl group R ⁶ to R ¹⁰ each independently represent a hydrogen atom, a halogen atom, an alkyl group having a carbon number of 1-6, methoxy group, having 1 to 3 carbon atoms in the alkyl carbonyl amino group or -SO ₃ ^- shows the However, at least one of R ⁶ to R ¹⁰ represents -SO ₃ ^- )

A coloring composition for color filters containing a methine compound represented by, a binder resin, and a dispersant.

(2) R ¹ to R ⁴ are each independently a hydrogen atom, a halogen atom or an alkyl group having 1 to 4 carbon atoms, and either one of R ⁷ and R ⁹ is -SO ₃ ^- and the other is a hydrogen atom, a halogen atom, The coloring composition for color filters according to the preceding item (1), which is an alkyl group having 1 to 6 carbon atoms, a methoxy group or an alkylcarbonylamino group having 1 to 3 carbon atoms.

(3) The coloring composition for color filters according to the preceding item (1) or (2), wherein the dispersant contains an acrylic dispersant.

(4) The colored composition for color filters according to any one of the preceding items (1) to (3), which further contains a pigment.

(5) The coloring composition for color filters according to the preceding item (4), wherein the pigment contains a pigment having a phthalocyanine structure.

(6) A color filter obtained using the colored composition according to any one of the preceding items (1) to (5).

(7) A liquid crystal display device, an organic EL display, or a solid-state imaging device equipped with the color filter according to the preceding item (6).

By using the colored composition for color filters of the present invention, it is possible to provide a green pixel of a high-quality and reliable color filter excellent in brightness.

(Form for carrying out the invention)

The colored composition for color filters of the present invention (hereinafter, also simply referred to as "coloring composition") contains a methine compound represented by the above formula (1).

In formula (1), R ¹ to R ⁴ each independently represent a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms, a methoxy group, or a nitro group.

Examples of the halogen atom represented by R ¹ to R ⁴ in the formula (1) include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, and a chlorine atom is preferable.

Examples of the alkyl group having 1 to 4 carbon atoms represented by R ¹ to R ⁴ in formula (1) include methyl group, ethyl group, n-propyl group, iso-propyl group, n-butyl group, iso-butyl group, sec-butyl group and tert -Butyl group is mentioned, and a methyl group is preferable.

As R ¹ to R ^{4 in} formula (1), it is preferable that each independently a hydrogen atom, a halogen atom, or an alkyl group having 1 to 4 carbon atoms. It is more preferable that two or three selected from R ¹ to R ⁴ are hydrogen atoms, and each other is independently a hydrogen atom, a halogen atom, or an alkyl group having 1 to 4 carbon atoms. R ⁴ is a hydrogen atom, one or two selected from R ¹ to R ³ are hydrogen atoms, and it is more preferable that the others are each independently a hydrogen atom, a halogen atom or an alkyl group having 1 to 4 carbon atoms, and R ⁴ is a hydrogen atom, one or two selected from R ¹ to R ³ are hydrogen atoms, and it is particularly preferable that the other is a halogen atom or an alkyl group having 1 to 4 carbon atoms, R ⁴ is a hydrogen atom, and R It is most preferred that one or two selected from ¹ to R ³ are hydrogen atoms, and the other is an alkyl group having 1 to 4 carbon atoms.

In formula (1), R ⁵ represents an alkyl group having 1 to 4 carbon atoms, a methoxyethyl group, or a butoxyethyl group.

As R ^{5 in} formula (1), it is preferable that it is a C1-C4 alkyl group.

Examples of the alkyl group having 1 to 4 carbon atoms represented by R ⁵ in the formula (1) include the same alkyl groups having 1 to 4 carbon atoms represented by R ¹ to R ⁴ in the formula (1). A methyl group is preferred.

In formula (1), R ⁶ to R ¹⁰ each independently represent a hydrogen atom, a halogen atom, an alkyl group having 1 to 6 carbon atoms, a methoxy group, an alkylcarbonylamino group having 1 to 3 carbon atoms, or -SO ₃ ^- . However, at least one of R ⁶ to R ¹⁰ represents -SO ₃ ^- .

Examples of the halogen atom represented by R ⁶ to R ¹⁰ in the formula (1) include the same halogen atom as the halogen atom represented by R ¹ to R ⁴ in the formula (1), and a chlorine atom, a bromine atom or an iodine atom is preferable. A chlorine atom is more preferable.

The alkyl group having 1 to 6 carbon atoms represented by R ⁶ to R ^{10 in} formula (1) is not limited to either linear, branched or cyclic as long as it is an alkyl group having 1 to 6 carbon atoms. Specific examples thereof include methyl group, ethyl group, n-propyl group, iso-propyl group, n-butyl group, iso-butyl group, sec-butyl group, tert-butyl group, n-pentyl group, 1-methylbutyl group, 2 -Methylbutyl group, 3-methylbutyl group, 1-ethylpropyl group, 1,1-dimethylpropyl group, 1,2-dimethylpropyl group, 2,2-dimethylpropyl group, n-hexyl group, 1-methylphene Tyl group, 2-methylpentyl group, 3-methylpentyl group, 4-methylpentyl group, 1,1-dimethylbutyl group, 1,2-dimethylbutyl group, 1,3-dimethylbutyl group, 2,2-dimethylbutyl Group, 2,3-dimethylbutyl group, 3,3-dimethylbutyl group, 1-ethyl-1-methylpropyl group, and cyclohexyl group.

Examples of the alkylcarbonylamino group having 1 to 3 carbon atoms represented by R ⁶ to R ^{10 in} formula (1) include a methylcarbonylamino group, an ethylcarbonylamino group, an n-propylcarbonylamino group, and an iso-propylcarbonylamino group. . A methylcarbonylamino group or an iso-propylcarbonylamino group is preferred.

As R ⁶ to R ^{10 in} formula (1), R ⁷ or R ⁹ is -SO ₃ ^-, and each independently a hydrogen atom, a halogen atom, an alkyl group having 1 to 6 carbon atoms, a methoxy group or a carbon number of 1 to It is preferably an alkylcarbonylamino group of 3. R ⁶ and R ¹⁰ are a hydrogen atom, R ⁷ or R ⁹ is -SO ₃ ^- , and the others are each independently a hydrogen atom, a halogen atom, an alkyl group having 1 to 6 carbon atoms, a methoxy group or a carbon number of 1 to 3 It is more preferable that it is an alkylcarbonylamino group. R ⁶ and R ¹⁰ is a hydrogen atom, R ⁷ or R ⁹ is -SO ₃ ^-, and each of the others is independently a hydrogen atom, a halogen atom, a methoxy group, or an alkylcarbonylamino group having 1 to 3 carbon atoms. Preferably, R ⁶ and R ¹⁰ are a hydrogen atom, one of R ⁷ and R ⁹ is -SO ₃ ^- and the other is a hydrogen atom, and R ⁸ is a hydrogen atom, a halogen atom, a methoxy group, or 1 to C 1 It is particularly preferable that it is an alkylcarbonylamino group of 3, R ⁶ and R ¹⁰ are hydrogen atoms, one of R ⁷ and R ⁹ is -SO ₃ ^- , the other is a hydrogen atom, and R ⁸ is a halogen atom. It is most preferred.

As the methine compound represented by formula (1) contained in the coloring composition of the present invention, a combination of the preferable ones of each of R ¹ to R ¹⁰ is more preferable, and a combination of the more preferable ones of each of R ¹ to R ¹⁰ is furthermore desirable.

The methine compound represented by formula (1) contained in the coloring composition of the present invention can be produced by various methods. For example, it can be manufactured by the following method with reference to the method described in patent document 7. In addition, R ¹ to R ¹⁰ in the following formulas (AA) to (D) each represent the same meaning as R ¹ to R ¹⁰ in the formula (1).

First, a compound represented by the following formula (AA) available as a commercial product is used with an alkoxyalkylating agent such as methoxyethyl p-toluenesulfonic acid and butoxyethyl p-toluenesulfonic acid, or an alkylating agent such as alkyl p-toluenesulfonic acid and dialkylsulfonic acid. By reacting, it converts into a derivative represented by the following formula (B). Then, it is converted into a formyl derivative represented by the following formula (C) by a conventional Vilsmeier reaction.

On the other hand, by condensation reaction of a compound represented by the following formula (D) available as a commercial product with a formyl derivative represented by the formula (C), a corresponding methine compound represented by the above formula (1) can be obtained.

The reaction temperature in the condensation step is preferably 20 to 60°C, more preferably 30 to 50°C.

As the solvent used in the condensation step, for example, methanol, ethanol, n-propanol, iso-propanol, n-butanol, iso-butanol, N-methylpyrrolidone (hereinafter abbreviated as NMP), water, Hydrochloric acid water, sulfuric acid water, acetic acid and propionic acid are preferred. These can be used alone or in combination.

In the above condensation step, an acid catalyst may be added. Specific examples of the acid catalyst include inorganic acids such as hydrochloric acid and sulfuric acid, and Lewis acids such as aluminum chloride.

Below, although the specific example of the methine compound represented by Formula (1) is shown, the methine compound represented by Formula (1) contained in the coloring composition of this invention is not limited to these.

The content of the methine compound represented by formula (1) in the coloring composition of the present invention is usually 0.5 to about the total solid content of the coloring composition of the present invention (total components other than the solvents contained in the coloring composition of the present invention). It is 50 mass %, Preferably it is 1 to 30 mass %.

Further, in the coloring composition of the present invention, a plurality of types of methine compounds contained in formula (1) may be used in combination. When used in combination, the total amount of the methine compound contained in the formula (1) may be an amount within the above range.

The colored composition of the present invention contains a binder resin. The binder resin contained in the colored composition is not particularly limited, and conventionally known ones are mentioned. In the case of using the colored composition of the present invention by the method of photolithography, ethylenically unsaturated monomers having at least one carboxyl group or hydroxyl group as exemplified below, or ethylenically unsaturated monomers having other copolymerizable aromatic hydrocarbon groups or aliphatic hydrocarbon groups, etc. It is preferably a copolymer. In addition, those having an epoxy group on the side chains or terminals thereof, and an epoxy acrylate resin to which an acrylate is further added can also be used. These monomers may be used alone or in combination of two or more.

Specific examples of the ethylenically unsaturated monomer having a carboxyl group that can be used in the present invention include unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, α-chloroacrylic acid, ethacrylic acid, and cinnamic acid; Unsaturated dicarboxylic acids (anhydrides) such as maleic acid, maleic anhydride, fumaric acid, itaconic acid, itaconic anhydride, citraconic acid, citraconic anhydride, and mesaconic acid; Trivalent or higher unsaturated polyhydric carboxylic acids (anhydrides), 2-(meth)acryloyloxyethylhexahydrophthalic acid, 2-methacryloyloxyethyl2-hydroxypropylphthalate, 2-acryloyloxyethyl2- And hydroxyethylphthalic acid. These may be used alone or in combination of two or more.

Specific examples of the ethylenically unsaturated monomer having a hydroxyl group that can be used in the present invention include 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, and 3-hydroxypropyl (meth)acrylic. Rate, 4-hydroxybutyl (meth)acrylate, 3-hydroxybutyl (meth)acrylate, 5-hydroxypentyl (meth)acrylate, 4-hydroxypentyl (meth)acrylate, 3-hydroxy Pentyl (meth)acrylate, 6-hydroxyhexyl (meth)acrylate, 5-hydroxyhexyl (meth)acrylate, 4-hydroxyhexyl (meth)acrylate, 5-hydroxy-3-methyl-pentyl (Meth)acrylate, cyclohexane-1,4-dimethanol-mono(meth)acrylate, 2-(2-hydroxyethyloxy)ethyl (meth)acrylate, glycerin monomethacrylate, polyethylene glycol mono( And hydroxyl-terminated polyalkylene glycol mono(meth)acrylates such as meth)acrylate, polypropylene glycol mono(meth)acrylate, and poly(ethylene glycol-propylene glycol) monomethacrylate. These may be used alone or in combination of two or more.

In addition, as the above other copolymerizable ethylenically unsaturated monomers, for example, styrene, α-methylstyrene, o-vinyltoluene, m-vinyltoluene, p-vinyltoluene, o-chlorostyrene, m-chlorostyrene, p -Aromatic vinyl compounds such as chlorostyrene and p-methoxystyrene; Methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, iso-propyl (meth) acrylate, n-butyl (meth) acrylate, iso-butyl (meth) acrylate, sec-butyl (meth)acrylate, tert-butyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, benzyl (meth)acrylate, paracumylphenoxyethylene glycol (meth)acrylate, 2- Hydroxy-3-phenoxypropyl (meth)acrylate, o-phenylphenol glycidyl ether (meth)acrylate, o-phenylphenol (meth)acrylate hydroxyethyl product, phenoxyethyl (meth)acrylate Unsaturated carboxylic acid esters such as; Cyclopentyl (meth)acrylate, cyclohexyl (meth)acrylate, trimethylcyclohexyl (meth)acrylate, norbornyl (meth)acrylate, norbornylmethyl (meth)acrylate, phenylnorbornyl (meth) )Acrylate, cyanonorbornyl (meth)acrylate, isobornyl (meth)acrylate, bornyl (meth)acrylate, menthyl (meth)acrylate, pentyl (meth)acrylate, adamantyl ( Meth)acrylate, dimethyladamantyl(meth)acrylate, tricyclo[5.2.1.0 ^2,6 ]deca-8-yl=(meth)acrylate, tricyclo[5.2.1.0 ^2,6 ]deca-4 Alicyclic skeletons such as methyl=(meth)acrylate, cyclodecyl(meth)acrylate, 2-(meth)acryloyloxyethylhexahydrophthalic acid, and tert-butylcyclohexyl(meth)acrylate; Hydroxyl-terminated polyalkylene glycol mono(meth)acrylates such as polyethylene glycol mono(meth)acrylate, polypropylene glycol mono(meth)acrylate, and poly(ethylene glycol-propylene glycol) monomethacrylate; Methoxy polyethylene glycol monomethacrylate, lauroxy polyethylene glycol mono (meth) acrylate, octoxy polyethylene glycol polypropylene glycol mono (meth) acrylate, nonyl phenoxy polyethylene glycol monoacrylate, nonyl phenoxy polypropylene glycol mono Alkyl-terminated polyalkylene glycol mono(meth)acrylates such as acrylate and allyloxypolyethylene glycol-polypropylene glycol mono(meth)acrylate; Unsaturated carboxylic acid amino such as 2-aminoethyl acrylate, 2-aminoethyl methacrylate, 2-aminopropyl acrylate, 2-aminopropyl methacrylate, 3-aminopropyl acrylate, and 3-aminopropyl methacrylate Alkyl esters; Glycidyl acrylate, glycidyl methacrylate, 3,4-epoxybutyl (meth)acrylate, (3,4-epoxycyclohexyl)methyl (meth)acrylate, 4-hydroxybutyl (meth)acrylic Unsaturated carboxylic acid glycidyl esters such as late glycidyl ether; Vinyl carboxylic acid esters such as vinyl acetate, vinyl propionate, vinyl butyrate, and vinyl benzoate; Unsaturated ethers such as vinyl methyl ether, vinyl ethyl ether, allyl glycidyl ether, and methacryl glycidyl ether; Vinyl cyanide compounds such as acrylonitrile, methacrylonitrile, α-chloroacrylonitrile, and vinylidene cyanide; Acrylamide, methacrylamide, α-chloroacrylamide, N-phenylmaleimide, N-cyclohexylmaleimide, N-(meth)acryloylphthalimide, N-(2-hydroxyethyl)acrylamide, Unsaturated amides or unsaturated imides such as N-(2-hydroxyethyl)methacrylamide and maleimide; Aliphatic conjugated dienes such as 1,3-butadiene, isoprene, and chloroprene; Having a monoacryloyl group or a monomethacryloyl group at the end of a polymer molecular chain such as polystyrene, polymethylacrylate, polymethyl methacrylate, polyn-butyl acrylate, polyn-butyl methacrylate, and polysilicon Macromonomers, etc. are mentioned. These may be used alone or in combination of two or more.

Further, a polymer in which an unsaturated double bond is further introduced into the side chain of the copolymer is also useful. For example, acrylate or glycidyl having an alcoholic hydroxyl group such as hydroxyethyl acrylate in the maleic anhydride portion of a copolymer of styrene, vinylphenol, acrylic acid, acrylic acid ester, acrylamide, etc. that can be copolymerized with maleic anhydride Reaction of acrylic acid to the hydroxyl group of a compound obtained by reacting an acrylate having an epoxy group such as methacrylate to be half-esterified, and a copolymer of acrylic acid, an acrylate having an alcoholic hydroxyl group such as acrylic acid ester and hydroxyethyl acrylate The made compound etc. are mentioned. In addition, urethane resin, polyamide, polyimide resin, polyester resin, commercially available ACA-200M (manufactured by Daicel), ORGA-3060 (manufactured by Osaka Yuki Chemical), AX3-BNX02 (manufactured by Nihonshokubai), UXE- 3024 (manufactured by Nippongayaku), UXE-3000 (manufactured by Nippongayaku), ZGA-287H (manufactured by Nippongyaku), TCR-1338H (manufactured by Nippongyaku), ZXR-1722H (manufactured by Nippon Kayaku), ZFR- 1401H (manufactured by Nippongayaku) and ZCR-1642 (manufactured by Nippongayaku) can also be used.

When producing the binder resin (copolymer) contained in the colored composition of the present invention, a polymerization initiator is used. Specific examples of the polymerization initiator used when synthesizing the copolymer here include α,α'-azobis (isobutyronitrile), 2,2'-azobis (2-methylbutyronitrile), tert-butylper Octoate, di-tert-butyl peroxide and benzoyl methyl ethyl ketone peroxide peroxide. The use ratio of the polymerization initiator is 0.01 to 25 parts by mass with respect to 100 parts by mass in total of all monomers used in the synthesis of the copolymer. In addition, when synthesizing the copolymer, it is preferable to use an organic solvent described below, but one having sufficient solubility for the monofunctional monomer or polymerization initiator to be used is used. The reaction temperature when synthesizing the copolymer is preferably 50 to 120°C, more preferably 80 to 100°C. In addition, the reaction time is preferably 1 to 60 hours, more preferably 3 to 20 hours. The preferred acid value of the copolymer is 10 to 300 (mgKOH/g), and the preferred hydroxyl value is 10 to 200 (mgKOH/g). When the acid value or hydroxyl value is 10 or more, good developability can be obtained. The weight average molecular weight (Mw) of the copolymer is preferably 2,000 to 400,000, and more preferably 3,000 to 100,000. When the weight average molecular weight is 2,000 to 400,000, good sensitivity, developability, and the like can be obtained.

In addition, the acid value here is the method based on JIS K-2501, and the hydroxyl value means the value measured by the method based on JIS K-1557, respectively. The weight average molecular weight means a value calculated in terms of polystyrene based on the measurement result of gel permeation chromatography (GPC).

The above-described binder resin can be used alone or in combination of two or more in the colored composition of the present invention. The content of the binder resin in the colored composition of the present invention is usually 1 to 99% by mass, preferably 5 to 50% by mass with respect to the total solid content of the colored composition.

The coloring composition of the present invention contains a dispersant. Dispersants that can be used in combination with oil-soluble organic solvents include sodium dodecylbenzenesulfonate, sodium laurate, formalin condensate of naphthalenesulfonic acid, formalin condensate of alkylnaphthalenesulfonic acid, formalin condensate of creosote oil sulfonic acid, poly Known anionic surfactants such as ammonium salt of oxyethylene alkyl ether sulfate, ammonium salt of polyoxyethylene alkylphenyl ether sulfate, and polyoxyalkyl ether phosphoric acid ester salt, vinyl naphthalene derivative, aliphatic alcohol ester of α,β-ethylenically unsaturated carboxylic acid, etc. , Styrene, styrene derivatives, acrylic acid, acrylic acid derivatives, methacrylic acid, methacrylic acid derivatives, maleic acid, maleic acid derivatives, maleic anhydride, maleic anhydride derivative, itaconic acid, itaconic acid derivative, fumaric acid, fumaric acid derivative, etc. And polymer dispersants such as block copolymers or random copolymers composed of monomers, or salts thereof.

As a dispersant that can be used in combination with a water-soluble organic solvent or water, a polymer dispersant other than a surfactant can be suitably used. Specific examples of the polymer dispersant include polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acid, acrylic acid-acrylonitrile copolymer, acrylate-acrylonitrile copolymer, vinyl acetate-acrylic acid ester copolymer, acrylic acid-acrylic acid ester copolymer, etc. Acrylic resin, styrene-acrylic acid copolymer, styrene-methacrylic acid copolymer, styrene-methacrylic acid-acrylic acid ester copolymer, styrene-α-methylstyrene-acrylic acid copolymer, styrene-α-methylstyrene-acrylic acid-acrylic acid Styrene-acrylic resin such as ester copolymer, styrene-maleic acid copolymer, styrene-maleic anhydride copolymer, isobutylene-maleic acid resin, rosin-modified maleic acid resin, vinyl naphthalene-acrylic acid copolymer, vinyl naphthalene-maleic acid copolymer, and, Vinyl acetate-based copolymers such as vinyl acetate-ethylene copolymer, vinyl acetate-vinylethylene fatty acid copolymer, vinyl acetate-maleic acid ester copolymer, vinyl acetate-crotonic acid copolymer, and vinyl acetate-acrylic acid copolymer, and salts thereof. I can.

Further, examples of other resin-based dispersants include polyurethane resin-based, polycarboxylic acid-based, polyamide resin-based, and polyester resin-based dispersants. Specific examples of the resin-based dispersant include, for example, ED211 (manufactured by Kusumoto Kasei), Azisper PB821 (manufactured by Ajinomoto Fine Techno), Solsperse 71000 (manufactured by Avisia), and DISPERBYK-2001 (manufactured by Vicchemy Japan). .

These dispersants are usually 800% by mass or less, preferably, based on the total amount of pigments other than the methine compound represented by formula (1) contained in the coloring composition of the present invention and the methine compound represented by formula (1) optionally contained. Preferably, 10 to 700% by mass, more preferably 80 to 600% by mass is used.

The colored composition of the present invention may contain components other than the methine compound represented by the formula (1), the binder resin, and the dispersant (hereinafter, referred to as "other components").

Examples of the other components include solvents and resins such as oil-soluble organic solvents, water-soluble organic solvents and water, and further, various additives that can be used in combination with these solvents and resins. One or two or more of these can be used without particular limitation according to the use or usage of the coloring composition.

Specific examples of the oil-soluble organic solvent include alcohols such as ethanol, pentanol, octanol, cyclohexanol, benzyl alcohol, and tetrafluoropropanol; Ethylene glycol monoethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monoethyl ether, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, triethylene glycol monoethyl ether, ethylene glycol di Glycol derivatives such as acetate, propylene glycol monomethyl ether acetate, and propylene glycol diacetate; Ketones such as methyl ethyl ketone and cyclohexanone; Ethers such as butyl phenyl ether, benzyl ether, and hexyl ether; Esters such as ethyl acetate, butyl acetate, ethyl benzoate, butyl benzoate, ethyl laurate, and butyl laurate; Polar organic solvents such as acetonitrile, N,N-dimethylformamide (hereinafter abbreviated as DMF), dimethyl sulfoxide, sulfolane, NMP, and 2-pyrrolidone.

Examples of the water-soluble organic solvent include alcohols such as methanol, ethanol, propanol, isopropanol, butanol, isobutanol, tert-butanol, pentanol, and benzyl alcohol; Polyhydric alcohols such as ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, polyethylene glycol, polypropylene glycol, glycerin, trimethylolpropane, 1,3-pentanediol and 1,5-pentanediol; Glycol derivatives such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol monobutyl ether, triethylene glycol monoethyl ether, triethylene glycol monobutyl ether and dipropylene glycol monomethyl ether ; Amines such as ethanolamine, diethanolamine, triethanolamine, and morpholine; 2-pyrrolidone, NMP, 1,3-dimethyl-imidazolidinone, etc. are mentioned.

These solvents may be used alone or in combination of two or more. In the case of containing solvents, the amount used is preferably 40 to 1,0000 parts by mass, and more preferably 100 to 1,000 parts by mass, based on 100 parts by mass of the total solid content of the colored composition.

Examples of components other than the solvents that the colored composition of the present invention may contain include resins, curing agents, photoinitiators, thermal polymerization initiators, surface modifiers, antifoaming agents, antiseptic/antifogging agents, Pigments other than the pH adjuster and the methine compound represented by Formula (1), etc. are mentioned.

Examples of the resins that the colored composition of the present invention may contain include polyamide-based, polyurethane-based, polyester-based, epoxy-based, and polyacrylic resins.

The polyamide resin, polyurethane resin, polyester resin, epoxy resin, and polyacrylic resin that may be contained in the colored composition of the present invention are not particularly limited, and conventionally known ones may be mentioned.

Examples of the curing agent that the colored composition of the present invention may contain include a photopolymerization monomer in the case of radical polymerization, an epoxy resin in the case of ion curing, and other melamine curing agents. Specific examples of these are 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, ethylene glycol di (meth)acrylate, diethylene glycol Di(meth)acrylate, triethylene glycol(meth)acrylate, tetraethylene glycol(meth)acrylate, trimethylolpropane tri(meth)acrylate, pentaerythritol di(meth)acrylate, pentaerythritol tri( Meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol hexa(meth)acrylate, glycerol(meth)acrylate, bisphenol A type epoxy di(meth)acrylate, bisphenol F type epoxy di( Meth)acrylate, bisphenol fluorene type epoxy di(meth)acrylate, ethoxylated trimethylolpropane tri(meth)acrylate, propoxylated trimethylolpropane tri(meth)acrylate, ethoxylated glycerin tri(meth)acrylic Rate, ethoxylated isocyanuric acid tri(meth)acrylate, ditrimethylolpropanetetra(meth)acrylate, ethoxylated pentaerythritol tetra(meth)acrylate, 9,9-bis [4-(2-acrylic Royloxyethoxy) phenyl] fluorene, Kaylard RP-1040 (manufactured by Nippon Kayaku), Kayarad DPCA-30 (manufactured by Nippon Kayaku), UA-33H (manufactured by Shinnakamura Chemical), UA-53H ( Shinnakamura Kagaku), M-8060 (manufactured by Toagosei); As thiol-based polymerization monomers, TEMPIC (manufactured by Sakai Chemical), TMMP (manufactured by Sakai Chemical), PEMP (manufactured by Sakai Chemical), DPMP (manufactured by Sakai Chemical); As an epoxy resin, Nippon Kayaku's NC-6000, NC-3000, EOCN-1020, XD-1000, EPPN-501H, BREN-S, NC-7300L, Daisel Chemical's Celoxite 2021P, EHPE3150, Cyclomer M100, Epolide PB3600, Epicoat 828 manufactured by Japan Epoxy Resin, Epicoat YX8000, Epicoat YX4000, Sylar Ace S510 (manufactured by Chiso), TEPIC (manufactured by Nissan Chemical Co., Ltd.); Examples of the melamine curing agent include methylolated melamine and Mw-30 (manufactured by Sanwa Chemical). These can be used alone or in combination of two or more. Their content is usually 80 parts by mass or less, and preferably 5 to 30 parts by mass with respect to 100 parts by mass of the total solid content of the coloring composition.

As the photopolymerization initiator that the colored composition of the present invention may contain, it is preferable to have sufficient sensitivity to ultraviolet rays emitted from an ultra-high pressure mercury lamp generally used as an exposure light source. Examples thereof include a radical polymerizable photoradical initiator, an ion-curable photoacid generator, or a photobase generator. In photopolymerization, a component of a polymerization accelerator called a sensitizer can be used in combination to cure with less exposure energy. There is no particular limitation on the photoinitiator that can be used, but specific examples include benzyl, benzoin ether, benzoin butyl ether, benzoin propyl ether, benzophenone, 3,3'-dimethyl-4-methoxybenzophenone, and benzoylbenzoic acid. , Ester product of benzoylbenzoic acid, 4-benzoyl-4'-methyldiphenyl sulfide, benzyldimethylketal, 2-butoxyethyl-4-methylaminobenzoate, chlorothioxanthone, methylthioxanthone, ethylthioxane Tone, isopropyl thioxanthone, dimethyl thioxanthone, diethyl thioxanthone, diisopropyl thioxanthone, methylaminomethylbenzoate, 1-(4-dodecylphenyl)-2-hydroxy-2-methyl Propan-1-one, 1-hydroxycyclohexylphenylketone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, 1-(4-isopropylphenyl)-2-hydroxy-2- Methylpropan-1-one, methylbenzoyl formate, 2-methyl-1-(4-methylthiophenyl)-2-morpholinopropan-1-one, 2-benzyl-2-dimethylamino-1-(4 -Morpholinophenyl)-butanone-1,2,4-bis(trichloromethyl)-6-(4-methoxyphenyl)-1,3,5-s-triazine, 2,4,6- Tris(trichloromethyl)-1,3,5-s-triazine, 2,4-bis(tribromomethyl)-6-(4'-methoxyphenyl)-1,3,5-s-tri Azine, 2,4,6-tris(tribromomethyl)-1,3,5-s-triazine, 2,4-bis(trichloromethyl)-6-(1,3-benzodioxolane- 5-yl)-1,3,5-s-triazine, 1-(4-phenylsulfanylphenyl)butane-1,2-dione-2-oxime-o-benzoato, 1-(4-methylsulfur Panylphenyl)butane-1,2-dione-2-oxime-o-acetate, 1-(4-methylsulfanylphenyl)butan-1-oneoxime-o-acetate, 4,4'-bis(diethylamino ) Benzophenone, p-dimethylaminobenzoic acid isoamyl ester, p-dimethylaminobenzoic acid ethyl ester, 2,2'-bis(o-chlorophenyl)-4,4',5,5'-tetraphenyl-1,2 '-Bimidazole, diazonaphthoquinone initiator, also commercially available Kayacure DMBI, Kayacure BDMK, Kayacure BP-100, Kayacure BMBI, Kayacure DETX-S, Kayacure EPA (all manufactured by Nippon Kayaku) , Darocure 1173, Darocure 1116 (all manufactured by Merck Japan), Irgacure 907 (manufactured by BASF Japan), Irgacure 369 (manufactured by BASF Japan), Irgacure 379EG (manufactured by BASF Japan), Irgacure OXE-01 (manufactured by BASF Japan), Irgacure OXE-02 (manufactured by BASF Japan) , Irgacure PAG103 (manufactured by BASF Japan), TME-triazine (manufactured by Sanwa Chemical), biimidazole (manufactured by Kurogane Kasei), STR-110, STR-1 (all manufactured by Respe Chemical), and the like.

Examples of the thermal polymerization initiator that the colored composition of the present invention may contain include azo compounds and organic peroxides. For example, 2,2'-azobisisobutyronitrile, 2,2'-azobis (2,4-dimethylvaleronitrile), 2,2'-azobis (2-methylbutyronitrile), peroxidation Di-tert-butyl, dibenzoyl peroxide, cumyl peroxyneodecanoate, and the like.

These photoinitiators and thermal polymerization initiators can be used alone or in combination of two or more, as needed. The content of these initiators is usually 50 parts by mass or less, and preferably 1 to 25 parts by mass based on 100 parts by mass of the solid content of the colored composition.

As the surface modifier that the coloring composition of the present invention may contain, known nonionic nonionics such as polyoxyethylene sorbitan fatty acid ester, polyoxyethylene alkyl ether, polyoxyethylene alkylphenyl ether, copolymer of ethylene oxide and propylene oxide, etc. And polysiloxane-based or polydimethylsiloxane-based surfactants.

As the antifoaming agent, known antifoaming agents of silicone and acetylene are mentioned.

Preservatives and anti-foaming agents include sodium dehydroacetate, sodium benzoate, sodium pyridinethione-1-oxide, zinc pyridinethione-1-oxide, 1,2-benzisothiazolin-3-one, 1-benzisothiazoline-3 Known antiseptic and anti-foaming agents, such as an amine salt of -on, are mentioned.

Examples of the pH adjuster include known pH adjusters such as alkali metal hydroxides such as sodium hydroxide, potassium hydroxide and lithium hydroxide, tertiary amines such as triethanolamine, diethanolamine, dimethylethanolamine, and diethylethanolamine.

As a dye other than the methine compound represented by Formula (1) which the coloring composition of this invention may contain, an organic pigment, an inorganic pigment, a dye, etc. are mentioned.

In the case where a pigment such as an organic pigment or an inorganic pigment is used in the coloring composition of the present invention, the blending amount may be usually 0.5 to 50% by mass based on the total solid content of the coloring composition.

There is no particular limitation on the organic pigments that the coloring composition of the present invention may contain, but for example, anthraquinone-based, phthalocyanine-based, triphenylmethane-based, benzoimidazolone-based, quinacridone-based, azochelate-based, azo-based , Isoindolin-based, isoindolinone-based, pyrantrone-based, indanthrone-based, anthrapyrimidine-based, dibromoandanthrone-based, flavantron-based, perylene-based, perinone-based, quinophthalone-based, thioindigo-based Pigments such as dioxazine-based and xanthene-based; Lake pigments in which acid dyes, basic dyes, direct dyes, and the like are insolubilized with respective precipitating agents, dyeing lake pigments, etc. More specifically, in the color index, for example, Pigment Blue 1, 1:2, 9, 14, 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, 17, 19, 25, 27, 28, 29, 33, 35, 36, 56, 56:1, 60, 61, 61:1, 62, 63, 66, 67, 68, 71, 72, 73, 74, 75, 76, 78, 79; Pigment Violet 1, 1:1, 2, 2:2, 3, 3:1, 3:3, 4, 5, 5:1, 14, 15, 16, 19, 23, 25, 27, 29, 31 , 32, 37, 39, 42, 44, 47, 49, 50; Pigment Red 7, 14, 41, 48:1, 48:2, 48:3, 48:4, 57:1, 81, 81:1, 81:2, 81:3, 81:4, 81:5 , 122, 146, 168, 177, 178, 184, 185, 187, 200, 202, 208, 210, 246, 254, 255, 264, 270, 272, 279; Pigment Orange 43, 71, 73; Pigment Yellow 1, 2, 3, 4, 5, 6, 10, 12, 13, 14, 15, 16, 17, 18, 24, 31, 32, 34, 35, 35:1, 36, 36:1 , 37, 37: 1, 40, 42, 43, 53, 55, 60, 61, 62, 63, 65, 73, 74, 77, 81, 83, 93, 94, 95, 97, 98, 100, 101 , 104, 106, 108, 109, 110, 113, 114, 115, 116, 117, 118, 119, 120, 123, 126, 127, 128, 129, 138, 139, 147, 150, 151, 152, 153 , 154, 155, 156, 161, 162, 164, 166, 167, 168, 169, 170, 171, 172, 173, 174, 175, 176, 177, 179, 180, 181, 182, 185, 187, 188 , 193, 194, 198, 199, 213, 214; Pigment Green 7, 36, 58, 59, etc. are mentioned.

There are no particular restrictions on the inorganic pigments that the coloring composition of the present invention may contain, but for example, a complex metal oxide pigment, carbon black, black low-order titanium oxide, titanium oxide, barium sulfate, zinc oxide, Lead sulfate, lead yellow, bengala, ultramarine, royal blue, chromium oxide, antimony white, iron black, brisket, zinc sulfide, cadmium yellow, cadmium red, zinc, manganese, cobalt, carbonic acid And metal oxides such as magnesium, metal sulfides, sulfates, metal hydroxides, and metal carbonates.

There is no restriction|limiting in particular in the dye which the coloring composition of this invention can contain, An acidic dye, a basic dye, a direct dye, a sulfur dye, a vat dye, a naphthol dye, a reactive dye, and a disperse dye are mentioned. When an organic solvent is used together, it is preferable that it is soluble in an organic solvent, but it can be used suitably by setting it as a dispersion from a dye insoluble in an organic solvent. Dyes that are insoluble in organic solvents are well-known formulations.For example, in the case of acid dyes, organic amine compounds (e.g., n-propylamine, ethylhexylpropionic acid amine, etc.) are reacted to transform them into amine salt dyes, or It is known to react the same organic amine compound with its sulfonic acid group to modify it with a dye having a sulfonamide group or the like. These amine-modified dyes can also be used in the coloring composition of the present invention. As a specific dye thereof, in the color index, for example, C.I. Number of Acid Blue 1, 7, 9, 15, 18, 23, 25, 27, 29, 40, 42, 45, 51, 62, 70, 80, 83, 86, 87, 90, 92, 96, 103, 112, 113, 120, 129, 138, 147, 150, 158, 171, 182, 192, 210, 242, 243, 249, 256, 259, 267, 278, 280, 285, 290, 296, 315, 324, 335, 340; Basic Blue 7, 11, 15, 26; Solvent Blue 2, 3, 4, 5, 6, 23, 25, 35, 37, 38, 43, 55, 59, 67, 72, 124; Basic violet 10; Acid violet 17, 49; Solvent violet 4, 5, 14; Basic Red 1, 10, 29; Acid Red 91, 92, 97, 114, 138, 151, 289; Solvent red 45, 49, 127; Acid yellow 17, 23, 25, 29, 38, 40, 42, 76; Solvent Yellow 4, 14, 15, 24, 76, 81, 82, 94, 98, 162; Solvent orange 2, 7, 11, 15, 26, 56; Acid green 9, 16, and the like.

The colored composition of the present invention is prepared by mixing and stirring a methine compound represented by formula (1), a binder resin, and other components with a dissolver or a homomixer. When a pigment or a dye having low solubility is used in combination, a dispersion obtained by a dispersing machine such as a paint shaker may be added to the coloring composition and mixed with an appropriate dispersant. In order to remove foreign matters and the like from the prepared colored composition, microfiltration may be performed with a filter or the like.

The coloring composition of the present invention is used for various paints, aqueous inks, oil-based inks, inkjet inks, and coloring compositions for color filters. As a specific use of the colored composition for color filters, a color filter such as a solid-state imaging device used in a liquid crystal display device, an organic EL display, or a digital camera, etc. may be mentioned.

Examples of the material to be colored using the colored composition of the present invention include plain paper, coated paper, plastic film, and plastic substrate, but are not limited thereto. In addition, as a method of applying the colored composition of the present invention to a material to be colored, various printing methods such as offset printing, convex printing, flexographic printing, and inkjet printing, or a coating method using a spin coater or a roll coater may be mentioned.

As a method of manufacturing a color filter using the colored composition of the present invention, a dyeing method, an electrodeposition method, a printing method, a pigment dispersion method, and the like can be mentioned. As a typical example, the pigment dispersion method using the method of patterning is mentioned. As a representative example of the patterning method, a photolithography method is used. Alternatively, a method of forming a color filter by applying a colored composition directly onto a substrate by an inkjet printer without interposing a mask can also be used.

(Example)

Hereinafter, the present invention will be described in more detail by examples, but the present invention is not limited to these examples. In addition, unless otherwise specified, "parts" and "%" in the text are based on mass, and the reaction temperature is internal temperature.

Synthesis Example 1 (Synthesis of a mixture of a methine compound represented by No. 4 and a methine compound represented by No. 8 of the above specific example)

(Step 1-1)

To a 500 ml 4-neck flask, 3,4-dimethylphenylhydrazine hydrochloride represented by the following formula (100) (manufactured by Tokyo Chemical Industry Co., Ltd.) 55 parts, 3-methyl-2-butanone (manufactured by Tokyo Chemical Industry Co., Ltd.) 32 parts, 62 parts of 95% sulfuric acid and 220 parts of ethanol were put, and it stirred at 78 degreeC for 2 hours. After cooling the reaction solution, water and toluene are added, the organic layer is washed with water, dehydrated with saturated brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure to form an intermediate compound represented by the following formula (101). Mixture) was obtained.

(Step 1-2)

To a 300 ml four-necked flask, 44 parts of the intermediate compound represented by the formula (101) obtained in step 1-1, 88 parts of toluene, and 54 parts of dimethyl sulfate (manufactured by Tokyo Chemical Industry Co., Ltd.) were placed, and stirred at 90°C for 2 hours. After cooling the reaction solution to room temperature, 70 parts of water and 34 parts of potassium hydroxide were added, followed by stirring at 50°C for 1 hour. The organic layer was washed with water, dehydrated with saturated brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure to obtain 42 parts of an intermediate compound (a mixture of two types of compounds) represented by the following formula (102).

(Step 1-3)

In a 200 ml beaker, 58 parts of DMF were put, and 30 parts of phosphoryl chloride (manufactured by Junsei Chemical Co., Ltd.) were added dropwise while maintaining the liquid temperature at 10°C or less. To this, 40 parts of the intermediate compound represented by the formula (102) obtained in step 1-2 was added, and the mixture was stirred at 40°C for 1 hour. After cooling the reaction solution to room temperature, the reaction solution was poured into ice water, and a 25% aqueous sodium hydroxide solution was added until the pH reached 10. Furthermore, it heated to 80 degreeC, and after crystal|crystallization precipitated, the reaction liquid was cooled to room temperature. The precipitated crystal was filtered off, washed, and dried to obtain 37 parts of an intermediate compound (a mixture of two types of compounds) represented by the following formula (103).

(Step 1-4)

To a 3,000 ml beaker, 1,400 parts of methanol, 105 parts of the intermediate compound represented by the above formula (103) obtained in Step 1-3, 95.05 parts of 4-chloroaniline-3-sulfonic acid (manufactured by Tokyo Chemical Industry Co., Ltd.), 460 parts of water, and 150 parts of acetic acid was put, and it stirred at 45 degreeC for 2 hours. The precipitated crystals were filtered off, washed, and dried to obtain 163 parts of a mixture of the methine compound represented by No. 4 and the methine compound represented by No. 8 of the specific example.

Synthesis Example A (synthesis of binder resin)

160 parts of methyl ethyl ketone, 10 parts of methacrylic acid, 33 parts of benzyl methacrylate and 1 part of α,α'-azobis (isobutyronitrile) were added to a 500 ml four-necked flask, and nitrogen gas was added for 30 minutes while stirring. It flowed into the flask. Then, it heated up to 80 degreeC and stirred as it is at 80-85 degreeC for 4 hours. After completion of the reaction, it was cooled to room temperature to obtain a colorless, transparent and uniform copolymer solution. This was precipitated in a 1:1 mixed solution of isopropyl alcohol and water, filtered, and a solid content was taken out and dried to obtain a binder resin. The obtained binder resin had a weight average molecular weight in terms of polystyrene of 18,000, and an acid value of 152 (mgKOH/g).

Example 1 (Preparation of the colored composition of the present invention)

C.I. Pigment Green 59/mixture of the methine compound represented by No.4 and the methine compound represented by No.8 obtained in Synthesis Example 1/DISPERBYK-2001 (manufactured by Vicchemy Japan)/propylene glycol monomethyl ether acetate/propylene glycol mono After mixing at a composition ratio of ethyl ether/the binder resin obtained in Synthesis A = 0.09 parts/0.03 parts/0.62 parts/19.0 parts/1.2 parts/3.9 parts, 50 parts of 0.3 mm zirconia beads were added, followed by treatment with a paint shaker for 2 hours. Did. The beads were removed by filtration, and the colored composition 1 of the present invention was obtained.

Example 2 (Production of the color filter of the present invention)

Using a spin coater, the colored composition 1 of the present invention obtained in Example 1 was applied onto a glass substrate, and then dried at 80° C. for 10 minutes to prepare a color filter (dye colored body 1) of the present invention.

Comparative Example 1 (Preparation of a colored composition for comparison)

A mixture of the methine compound represented by No. 4 and the methine compound represented by No. 8 obtained in Synthesis Example 1 was prepared in C.I. Except having changed to Pigment Yellow 185, it carried out similarly to Example 1, and obtained the coloring composition 1 for comparison.

Comparative Example 2 (Preparation of color filter for comparison)

Except having changed the coloring composition 1 of the present invention obtained in Example 1 to the coloring composition 1 for comparison obtained in Comparative Example 1, it was carried out in the same manner as in Example 2, and the color filter for comparison (the dye colored body 1 for comparison ) Was produced.

(Brightness evaluation)

Using an ultraviolet visible spectrophotometer UV-1700 (manufactured by Shimadzu Corporation), the spectral transmittance of the color filter of the present invention and the color filter for comparison obtained in Example 2 and Comparative Example 2 was measured, and the CIE of the C light source was The chromaticity coordinates of x and y and the brightness Y in the XYZ color system were evaluated. For the chromaticity x and y required in calculating the brightness Y, generally known chromaticity x and y described in Japanese Unexamined Patent Application Publication No. 2018-154781 were used. In addition, the larger the brightness Y, the higher the brightness and the better. The results are shown in Table 1.

From the results of Table 1, it is clear that the color filter produced by using the colored composition 1 of the present invention exhibits better brightness than the color filter for comparison produced by using the colored composition for comparison.

By using the colored composition for color filters of the present invention containing a methine compound having a specific structure represented by Formula (1), a binder resin, and a dispersant, a green pixel of a color filter excellent in brightness can be provided.

Claims (19)

Formula (1)

(In formula (1), R ¹ to R ⁴ each independently represent a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms, a methoxy group or a nitro group; R ⁵ is an alkyl group having 1 to 4 carbon atoms, methoxy It represents an ethyl group or a butoxy group; R ⁶ to R ¹⁰ are each independently a hydrogen atom, a halogen atom, an alkyl group having 1 to 6 carbon atoms, a methoxy group, having 1 to 3 carbon atoms in the alkyl carbonyl amino group or -SO ₃ ^- represents ; However, at least one of R ⁶ to R ¹⁰ represents -SO ₃ ^- )
A coloring composition for color filters containing a methine compound represented by, a binder resin, and a dispersant. The method of claim 1,
R ¹ to R ⁴ are each independently a hydrogen atom, a halogen atom, or an alkyl group having 1 to 4 carbon atoms, and one of R ⁷ and R ⁹ is -SO ₃ ^- and the other is a hydrogen atom, a halogen atom, or 1 to C A coloring composition for color filters, which is an alkyl group of 6, a methoxy group, or an alkylcarbonylamino group having 1 to 3 carbon atoms. The method according to claim 1 or 2,
The coloring composition for color filters, wherein the dispersant contains an acrylic dispersant. The method according to claim 1 or 2,
The coloring composition for color filters which further contains a pigment. The method of claim 3,
The coloring composition for color filters which further contains a pigment. The method of claim 4,
The coloring composition for color filters, wherein the pigment contains a pigment having a phthalocyanine structure. The method of claim 5,
The coloring composition for color filters, wherein the pigment contains a pigment having a phthalocyanine structure. A color filter obtained by using the colored composition according to claim 1 or 2. A color filter obtained by using the colored composition according to claim 3. A color filter obtained by using the colored composition according to claim 4. A color filter obtained by using the colored composition according to claim 5. A color filter obtained by using the colored composition according to claim 6. A color filter obtained by using the colored composition according to claim 7. A liquid crystal display device, an organic EL display, or a solid-state imaging device equipped with the color filter according to claim 8. A liquid crystal display device, an organic EL display, or a solid-state imaging device equipped with the color filter according to claim 9. A liquid crystal display device, an organic EL display, or a solid-state imaging device equipped with the color filter according to claim 10. A liquid crystal display device, an organic EL display, or a solid-state imaging device equipped with the color filter according to claim 11. A liquid crystal display device, an organic EL display, or a solid-state image sensor equipped with the color filter according to claim 12. A liquid crystal display device, an organic EL display, or a solid-state imaging device equipped with the color filter according to claim 13.